DE69513538T2 - Epoxidamin barrierüberzüge mit aryloxy- oder aryloatgruppen - Google Patents
Epoxidamin barrierüberzüge mit aryloxy- oder aryloatgruppenInfo
- Publication number
- DE69513538T2 DE69513538T2 DE69513538T DE69513538T DE69513538T2 DE 69513538 T2 DE69513538 T2 DE 69513538T2 DE 69513538 T DE69513538 T DE 69513538T DE 69513538 T DE69513538 T DE 69513538T DE 69513538 T2 DE69513538 T2 DE 69513538T2
- Authority
- DE
- Germany
- Prior art keywords
- groups
- polyamine
- coating
- coating according
- barrier
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 230000004888 barrier function Effects 0.000 title claims abstract description 95
- 238000000576 coating method Methods 0.000 claims abstract description 104
- 229920000768 polyamine Polymers 0.000 claims abstract description 57
- 150000001412 amines Chemical class 0.000 claims abstract description 28
- 239000005022 packaging material Substances 0.000 claims abstract description 27
- 239000000463 material Substances 0.000 claims description 71
- 239000011248 coating agent Substances 0.000 claims description 60
- 229920000647 polyepoxide Polymers 0.000 claims description 50
- -1 naphthalene compound Chemical class 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 229920000642 polymer Polymers 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 11
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 11
- 125000003700 epoxy group Chemical group 0.000 claims description 10
- 125000004957 naphthylene group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 7
- 229930185605 Bisphenol Natural products 0.000 claims description 6
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 150000001555 benzenes Polymers 0.000 claims 2
- 125000006294 amino alkylene group Chemical group 0.000 claims 1
- 150000004951 benzene Polymers 0.000 claims 1
- 125000001997 phenyl group Polymers [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000035699 permeability Effects 0.000 abstract description 47
- 239000004593 Epoxy Substances 0.000 abstract description 15
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract description 12
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract description 12
- 150000002148 esters Chemical class 0.000 abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 125000004104 aryloxy group Chemical group 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 36
- 229910052760 oxygen Inorganic materials 0.000 description 35
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 31
- 239000001301 oxygen Substances 0.000 description 31
- 239000007789 gas Substances 0.000 description 30
- 239000002904 solvent Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000008199 coating composition Substances 0.000 description 21
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 20
- 238000001723 curing Methods 0.000 description 20
- 239000001569 carbon dioxide Substances 0.000 description 18
- 229910002092 carbon dioxide Inorganic materials 0.000 description 18
- 239000010408 film Substances 0.000 description 17
- 239000010410 layer Substances 0.000 description 16
- 229920005989 resin Polymers 0.000 description 16
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- 239000000203 mixture Substances 0.000 description 15
- 229920003023 plastic Polymers 0.000 description 13
- 239000004033 plastic Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 235000013305 food Nutrition 0.000 description 10
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- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000004806 packaging method and process Methods 0.000 description 8
- 239000002952 polymeric resin Substances 0.000 description 8
- 229920000098 polyolefin Polymers 0.000 description 8
- 229920001155 polypropylene Polymers 0.000 description 8
- 229920001296 polysiloxane Polymers 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229920003002 synthetic resin Polymers 0.000 description 8
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- 239000004417 polycarbonate Substances 0.000 description 7
- 229920000515 polycarbonate Polymers 0.000 description 7
- 229920000139 polyethylene terephthalate Polymers 0.000 description 7
- 239000005020 polyethylene terephthalate Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 230000008901 benefit Effects 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 5
- NARVIWMVBMUEOG-UHFFFAOYSA-N 2-Hydroxy-propylene Natural products CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 description 5
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- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 239000004715 ethylene vinyl alcohol Substances 0.000 description 3
- RZXDTJIXPSCHCI-UHFFFAOYSA-N hexa-1,5-diene-2,5-diol Chemical compound OC(=C)CCC(O)=C RZXDTJIXPSCHCI-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
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- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 2
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- 238000012546 transfer Methods 0.000 description 2
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- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
- ZPANWZBSGMDWON-UHFFFAOYSA-N 1-[(2-hydroxynaphthalen-1-yl)methyl]naphthalen-2-ol Chemical compound C1=CC=C2C(CC3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 ZPANWZBSGMDWON-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-IDEBNGHGSA-N 2-butoxyethanol Chemical group [13CH3][13CH2][13CH2][13CH2]O[13CH2][13CH2]O POAOYUHQDCAZBD-IDEBNGHGSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- WPYCRFCQABTEKC-UHFFFAOYSA-N Diglycidyl resorcinol ether Chemical class C1OC1COC(C=1)=CC=CC=1OCC1CO1 WPYCRFCQABTEKC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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- 239000004793 Polystyrene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
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- 150000001408 amides Chemical class 0.000 description 1
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- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 1
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
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- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
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- 230000014759 maintenance of location Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/182—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents
- C08G59/184—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents with amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5033—Amines aromatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/048—Forming gas barrier coatings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1334—Nonself-supporting tubular film or bag [e.g., pouch, envelope, packet, etc.]
- Y10T428/1341—Contains vapor or gas barrier, polymer derived from vinyl chloride or vinylidene chloride, or polymer containing a vinyl alcohol unit
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
- Y10T428/1379—Contains vapor or gas barrier, polymer derived from vinyl chloride or vinylidene chloride, or polymer containing a vinyl alcohol unit
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31507—Of polycarbonate
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31786—Of polyester [e.g., alkyd, etc.]
- Y10T428/31797—Next to addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
- Y10T428/31913—Monoolefin polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31938—Polymer of monoethylenically unsaturated hydrocarbon
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Laminated Bodies (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35768794A | 1994-12-16 | 1994-12-16 | |
| PCT/US1995/012000 WO1996018669A1 (fr) | 1994-12-16 | 1995-09-21 | Enduits barriere a base d'epoxy-amine comportant des groupes aryloxy ou aryloate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69513538D1 DE69513538D1 (de) | 1999-12-30 |
| DE69513538T2 true DE69513538T2 (de) | 2000-05-18 |
Family
ID=23406629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69513538T Expired - Fee Related DE69513538T2 (de) | 1994-12-16 | 1995-09-21 | Epoxidamin barrierüberzüge mit aryloxy- oder aryloatgruppen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5637365A (fr) |
| EP (1) | EP0797608B1 (fr) |
| AT (1) | ATE186930T1 (fr) |
| AU (1) | AU3679995A (fr) |
| CA (1) | CA2206898C (fr) |
| DE (1) | DE69513538T2 (fr) |
| ES (1) | ES2141387T3 (fr) |
| WO (1) | WO1996018669A1 (fr) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5840825A (en) * | 1996-12-04 | 1998-11-24 | Ppg Incustries, Inc. | Gas barrier coating compositions containing platelet-type fillers |
| US5728439A (en) * | 1996-12-04 | 1998-03-17 | Ppg Industries, Inc. | Multilayer packaging material for oxygen sensitive food and beverage |
| US5962093A (en) * | 1997-10-22 | 1999-10-05 | The Dow Chemical Company | Thermally stable polyetheramines |
| US6652779B1 (en) | 1998-07-27 | 2003-11-25 | Pacific Wave Industries, Inc. | Polymers containing polyene-based second-order nonlinear optical chromophores and devices incorporating the same |
| US6348992B1 (en) | 1998-07-27 | 2002-02-19 | Pacific Wave Industries, Inc. | Sterically stabilized polyene-bridged second-order nonlinear optical chromophores and devices incorporating the same |
| US6616865B1 (en) | 1998-07-27 | 2003-09-09 | Pacific Wave Industries, Inc. | Sterically stabilized second-order nonlinear optical chromophores with improved stability and devices incorporating the same |
| US6333051B1 (en) | 1998-09-03 | 2001-12-25 | Supratek Pharma, Inc. | Nanogel networks and biological agent compositions thereof |
| AU754514B2 (en) * | 1998-10-29 | 2002-11-21 | Closure Medical Corporation | Polymeric containers for 1,1-disubstituted monomer compositions |
| US6723113B1 (en) * | 2000-01-19 | 2004-04-20 | Cordis Neurovascular, Inc. | Inflatable balloon catheter seal and method |
| US6994687B1 (en) * | 2000-01-19 | 2006-02-07 | Cordis Neurovascular, Inc. | Inflatable balloon catheter with purge mechanism and method |
| US6309757B1 (en) * | 2000-02-16 | 2001-10-30 | Ppg Industries Ohio, Inc. | Gas barrier coating of polyamine, polyepoxide and hydroxyaromatic compound |
| US6962670B1 (en) | 2000-08-16 | 2005-11-08 | Eastman Chemical Company | Determination of layer thickness or non-uniformity of layer thickness based on fluorophore additives |
| US6558585B1 (en) | 2000-11-02 | 2003-05-06 | Pacific Wave Industries, Inc. | Techniques for electrode poling of electro-optic polymers to eliminate poling induced optical loss and poling induced damage to electro-optic chromophores |
| CA2432511A1 (fr) * | 2000-12-21 | 2002-06-27 | Boris W. K. Chiu | Contenant modifie |
| EP1270206B1 (fr) | 2001-06-27 | 2005-11-02 | Mitsubishi Gas Chemical Company, Inc. | Film multicouche absorbant l'oxygène |
| AU2002328410B2 (en) * | 2001-09-05 | 2008-06-26 | Mitsubishi Gas Chemical Company, Inc. | Adhesive for gas barrier laminates and laminated films |
| US6777088B2 (en) | 2002-04-01 | 2004-08-17 | Air Products And Chemicals, Inc. | Packaging materials having barrier coatings based on water-epoxy resin copolymers |
| ES2263868T3 (es) | 2002-04-04 | 2006-12-16 | Mitsubishi Gas Chemical Company, Inc. | Acero revestido con material organico con excelentes prestaciones que evitan la oxidacion y que evitan la corrosion y metodo para evitar la oxidacion del metal. |
| EP1352933B1 (fr) * | 2002-04-08 | 2011-06-08 | Mitsubishi Gas Chemical Company, Inc. | Film flexible imperméable au gaz |
| ES2250891T3 (es) | 2002-04-15 | 2006-04-16 | The Coca-Cola Company | Composicion revestimiento que contiene un aditivo epoxidico y estructuras revestidas con el mismo. |
| KR100863468B1 (ko) * | 2002-04-30 | 2008-10-16 | 미츠비시 가스 가가쿠 가부시키가이샤 | 기체 차단성을 갖는 코팅용 조성물, 이것을 사용하는 기체차단성을 갖는 코팅물 및 코팅된 필름 |
| DE60307728T2 (de) | 2002-06-25 | 2006-12-21 | Mitsubishi Gas Chemical Co., Inc. | Kraftstoffsystem mit ausgezeichneten Dichtigkeitseigenschaften |
| CN100343046C (zh) * | 2002-06-25 | 2007-10-17 | 三菱瓦斯化学株式会社 | 气体屏蔽性容器 |
| EG23499A (en) * | 2002-07-03 | 2006-01-17 | Advanced Plastics Technologies | Dip, spray, and flow coating process for forming coated articles |
| DE20211075U1 (de) * | 2002-07-22 | 2003-12-11 | Rpc Bramlage Gmbh | Behälterförmige Verpackungen |
| US7091162B2 (en) * | 2003-07-03 | 2006-08-15 | Johnsondiversey, Inc. | Cured lubricant for container coveyors |
| US20050145138A1 (en) * | 2003-12-30 | 2005-07-07 | Council Of Scientific And Industrial Research | Oxygen barrier material for packaging |
| MXPA06011806A (es) | 2004-04-16 | 2006-12-15 | Advanced Plastics Technologies | Articulos de mono y multiples capas y metodos de extrusion para producir los mismos. |
| US8541078B2 (en) * | 2004-08-06 | 2013-09-24 | Societe Bic | Fuel supplies for fuel cells |
| US7371459B2 (en) * | 2004-09-03 | 2008-05-13 | Tyco Electronics Corporation | Electrical devices having an oxygen barrier coating |
| US20060127616A1 (en) * | 2004-12-10 | 2006-06-15 | Graham Packaging Company, L.P. | Controlled infrared/fluid coating cure process |
| WO2006085063A1 (fr) * | 2005-02-09 | 2006-08-17 | Breath Limited | Scellement de récipients en plastique |
| KR20080003882A (ko) * | 2005-04-18 | 2008-01-08 | 어드밴스드 플라스틱스 테크놀로지즈 룩셈부르크 에스.에이. | 방수 코팅된 물품 및 그 제조 방법 |
| BRPI0617873A2 (pt) * | 2005-10-14 | 2011-08-09 | Advanced Plastics Technologies Lux Sa | métodos de formar artigos de multicamadas por aplicações de tratamento superficial |
| EP2001924A1 (fr) * | 2006-03-30 | 2008-12-17 | National Starch and Chemical Investment Holding Corporation | Agents d'étanchéité à barrière époxy-amines thermodurcissables |
| US20070269658A1 (en) * | 2006-05-05 | 2007-11-22 | Kondos Constantine A | Solvent-borne coating compositions, related methods and substrates |
| US7892396B2 (en) | 2006-06-07 | 2011-02-22 | Zephyros, Inc. | Toughened activatable material for sealing, baffling or reinforcing and method of forming same |
| DE102009027329A1 (de) * | 2009-06-30 | 2011-01-05 | Henkel Ag & Co. Kgaa | 2-Komponenten Kaschierklebstoff |
| US10894625B1 (en) | 2020-07-29 | 2021-01-19 | Verre Vert, Inc. | Lightweight polymer bottle for wine and spirits |
| US12012253B1 (en) | 2023-03-02 | 2024-06-18 | Verre Vert, Inc. | Lightweight polymer wine bottle suitable for use with natural cork or synthetic stoppers |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL215804A (fr) * | 1956-03-28 | |||
| US3592946A (en) * | 1968-03-05 | 1971-07-13 | Us Navy | Flexible amine-epoxide resin and the controlled temperature preparation thereof |
| US3635843A (en) * | 1969-07-17 | 1972-01-18 | Shell Oil Co | Crystalline 1,5-diglycidylnaphthalene and cured products thereof |
| JPS58152845A (ja) * | 1982-03-08 | 1983-09-10 | Mitsubishi Gas Chem Co Inc | 新規なポリアミン |
| US4908272A (en) * | 1987-04-27 | 1990-03-13 | Mitsubishi Gas Chemical Company, Inc. | Gas-barrier multilayered structure |
| US4847011A (en) * | 1987-10-09 | 1989-07-11 | Shell Oil Company | Bis-anthrols and bis-naphthols and diglycidyl ethers thereof |
| US5300541A (en) * | 1988-02-04 | 1994-04-05 | Ppg Industries, Inc. | Polyamine-polyepoxide gas barrier coatings |
| DE68922416T2 (de) * | 1988-02-04 | 1996-02-01 | Ppg Industries Inc | Ungelierte Polyamine-Polyepoxy Harze. |
| ES2116261T3 (es) * | 1988-02-04 | 1998-07-16 | Ppg Industries Inc | Capa intermedia de barrera. |
| US5006381A (en) * | 1988-02-04 | 1991-04-09 | Ppg Industries, Inc. | Ungelled polyamine-polyepoxide resins |
| US5008137A (en) * | 1988-02-04 | 1991-04-16 | Ppg Industries, Inc. | Barrier coatings |
| US5028462A (en) * | 1989-07-21 | 1991-07-02 | Amoco Corporation | Molded bottles and method of producing same |
| US4983719A (en) * | 1989-07-21 | 1991-01-08 | General Electric Company | Amorphous polyamide having excellent oxygen barrier properties from para-xylylene diamine, isophthalic acid and adipic acid |
| ES2113366T3 (es) * | 1990-10-03 | 1998-05-01 | Dow Chemical Co | Polieteraminas con funciones hidroxilo como capas de barrera para materiales sensibles al oxigeno. |
-
1995
- 1995-09-21 EP EP95934473A patent/EP0797608B1/fr not_active Expired - Lifetime
- 1995-09-21 DE DE69513538T patent/DE69513538T2/de not_active Expired - Fee Related
- 1995-09-21 CA CA002206898A patent/CA2206898C/fr not_active Expired - Fee Related
- 1995-09-21 ES ES95934473T patent/ES2141387T3/es not_active Expired - Lifetime
- 1995-09-21 AT AT95934473T patent/ATE186930T1/de not_active IP Right Cessation
- 1995-09-21 WO PCT/US1995/012000 patent/WO1996018669A1/fr active IP Right Grant
- 1995-09-21 AU AU36799/95A patent/AU3679995A/en not_active Abandoned
-
1996
- 1996-03-22 US US08/620,180 patent/US5637365A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0797608B1 (fr) | 1999-11-24 |
| ES2141387T3 (es) | 2000-03-16 |
| CA2206898C (fr) | 2001-01-09 |
| DE69513538D1 (de) | 1999-12-30 |
| CA2206898A1 (fr) | 1996-06-20 |
| ATE186930T1 (de) | 1999-12-15 |
| US5637365A (en) | 1997-06-10 |
| WO1996018669A1 (fr) | 1996-06-20 |
| AU3679995A (en) | 1996-07-03 |
| EP0797608A1 (fr) | 1997-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |